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$56+ Cheap flights from Kentucky to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:22 pm
TYS
-
MDW
Nonstop1h 35m
Allegiant Air
Thu 5/282:47 pm
MDW
-
TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/11$132
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:35 am
SDF
-
ORD
Nonstop1h 44m
United Airlines
Sat 3/145:50 pm
ORD
-
SDF
Nonstop1h 24m
United Airlines
Deal found 2/8$137
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:22 pm
TYS
-
MDW
Nonstop1h 35m
Allegiant Air
Sun 5/312:47 pm
MDW
-
TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/11$138
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/241:22 pm
TYS
-
MDW
Nonstop1h 35m
Allegiant Air
Thu 5/282:47 pm
MDW
-
TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/11$139
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:22 pm
TYS
-
MDW
Nonstop1h 35m
Allegiant Air
Sun 5/242:47 pm
MDW
-
TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/9$144
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/241:22 pm
TYS
-
MDW
Nonstop1h 35m
Allegiant Air
Sun 5/312:47 pm
MDW
-
TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/11$145
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:00 am
SDF
-
ORD
Nonstop1h 40m
American Airlines
Sat 5/166:57 pm
ORD
-
SDF
Nonstop1h 33m
American Airlines
Deal found 2/8$147
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:22 pm
TYS
-
MDW
Nonstop1h 34m
Allegiant Air
Sun 7/52:48 pm
MDW
-
TYS
Nonstop1h 30m
Allegiant Air
Deal found 2/9$156
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:00 am
SDF
-
ORD
Nonstop1h 44m
United Airlines
Wed 3/117:40 pm
ORD
-
SDF
Nonstop1h 33m
United Airlines
Deal found 2/10$177
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:55 am
SDF
-
MDW
Nonstop1h 20m
Southwest
Wed 3/116:15 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Deal found 2/10$177
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
SDF
-
ORD
Nonstop1h 40m
American Airlines
Sat 5/28:02 am
ORD
-
SDF
Nonstop1h 41m
American Airlines
Deal found 2/8$181
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:33 am
SDF
-
ORD
Nonstop1h 42m
American Airlines
Tue 3/172:52 pm
ORD
-
SDF
Nonstop1h 26m
American Airlines
Deal found 2/10$184

Find flight deals from Kentucky to Chicago

Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Kiwi.com)

One-way from

$56
(Southwest)

Popular in

January

Cheapest in

November

Average price

$295

Good round-trip deal

$106 or less

Good one-way deal

$190 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
Search Deals
From Kentucky to Chicago (CHI)
Search Deals
One-way flight from Kentucky to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Kentucky to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Kentucky to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Fly from

Kentucky

Fly to

Chicago

Route

Depart

Return

Price

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 3/7

5:35 am-6:19 am

Nonstop1h 44m

Chicago O'Hare Intl

Sat 3/14

5:50 pm-8:14 pm

Nonstop1h 24m

$137

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 3/11

11:50 am-12:05 pm

Nonstop1h 15m

Chicago Midway

Wed 3/11

6:15 pm-8:30 pm

Nonstop1h 15m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 3/17

7:05 pm-7:25 pm

Nonstop1h 20m

Chicago Midway

Wed 3/18

6:15 pm-8:30 pm

Nonstop1h 15m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 3/10

7:05 pm-7:25 pm

Nonstop1h 20m

Chicago Midway

Wed 3/11

3:35 pm-11:30 pm

1 stop6h 55m

$187

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Tue 3/10

4:22 pm-5:02 pm

Nonstop1h 40m

Chicago O'Hare Intl

Tue 3/17

1:28 pm-3:51 pm

Nonstop1h 23m

$189

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 3/4

8:05 am-6:40 pm

2 stops11h 35m

Chicago Midway

Mon 3/9

9:35 am-1:31 pm

1 stop2h 56m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 3/27

10:27 am-11:02 am

Nonstop1h 35m

Chicago O'Hare Intl

Sun 3/29

8:49 pm-11:16 pm

Nonstop1h 27m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 5/14

7:00 am-7:50 am

Nonstop1h 50m

Chicago O'Hare Intl

Sun 5/17

5:45 pm-8:14 pm

Nonstop1h 29m

$189

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 4/13

6:19 pm-11:59 pm

1 stop6h 40m

Chicago O'Hare Intl

Wed 4/15

1:36 pm-12:11 am

2 stops9h 35m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 3/5

5:07 pm-5:47 pm

Nonstop1h 40m

Chicago O'Hare Intl

Sun 3/8

7:04 am-9:28 am

Nonstop1h 24m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Chicago

What is the cheapest month to book a flight from Kentucky to Chicago?

Currently, September is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $77). Flying from Kentucky to Chicago in July is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from KY to CHI?

Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.

One of the essential ways to save on airfare from Kentucky to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 34% on airfare.

What is the cheapest day to fly from Kentucky to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Chicago. Price data was last updated on February 7, 2026.

Travelers seeking maximum savings on their Kentucky to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Kentucky to Chicago

Explore weekly flight availability from Kentucky to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 12, 2026.

The most flights from USKY to CHI are scheduled on a Wednesday (35 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Kentucky to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Kentucky to Chicago?

    There are many flights that can get you from Kentucky to Chicago in 1h 20m. Fly via United Airlines, Southwest, or American Airlines to get the fastest option. The distance from Kentucky to Chicago is about 271 mi. Most flights are nonstop.

  • What are the cheapest airlines to fly from Kentucky to Chicago one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $38. American Airlines flights start at $52 while deals on United Airlines start at $53 one-way.

  • What are the most popular routes from Kentucky to Chicago?

    The most popular flight routes from Kentucky to Chicago are Nashville Intl - Chicago O'Hare Intl, Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl and Nashville Intl - Chicago Midway.

  • What are the most reliable airlines from Kentucky to Chicago?

    Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Iberia (86%), Copa Airlines (86%), Qatar Airways( 80%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $1,083 for a flight from Kentucky to Chicago. The cheapest flight overall is $111 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $143.

  • Can I find deals for flights from Kentucky to Chicago that include hotel bookings?

    Yes. In addition to deals on Kentucky to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kentucky to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Chicago.

  • Can I find deals for business class flights from Kentucky to Chicago?

    Yes. Cheapflights offers flight deals from Kentucky to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kentucky to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $77). Flying from Kentucky to Chicago in July is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Kentucky to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Kentucky to Chicago

Discover the top 4 airlines that operate flights from Kentucky to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$97Average$271FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$97Average$268FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$257FlexibilityNo cancel feeOn-time63%
ContourCheapest$108Average$163FlexibilityNo cancel feeOn-timeN/A

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